Three Successful Serial Entrepreneurs

Over the years, multiple studies have shown that the majority of entrepreneurs who fail with a business venture will never try to launch another one in the future. And with failure rates so high for first-time entrepreneurs, this means only a very small fraction of people are ever successful enough to grow multiple startups into thriving companies. This special subset includes folks like:

1. Richardson Branson

When you hear the term “serial entrepreneur,” Richard Branson is someone who often comes to mind. He’s the founder of the massive business conglomerate Virgin Group, which owns more than 200 businesses in industries such as manufacturing, music, professional sports, healthcare, energy and more.

2. Jeff Kinney

You may not recognize the name, but you’ll recognize his work. Jeff Kinney is the mastermind behind the best-selling "Diary of a Wimpy Kid" book series. Not only has he authored a handful of books, but he’s also turned some of these books into films, and acted in them. Additionally, he’s the creator of the child-friendly gaming site Poptropica. As an author, game designer, and actor, you can officially call him a modern day Renaissance man.

3. Michael Rubin

Being a serial entrepreneur means always looking for the next opportunity, even if you’re currently busy with one. This is a concept Michael Rubin understands well. Before ever going to college, he acquired a chain of ski-shops in Pennsylvania. Since then, he’s founded more than five sports-related businesses, including Fanatics, Inc. and ShopRunner. He’s also invested in the New Jersey Devils and the Philadelphia 76ers.

While each of these entrepreneurs works in a different industry and enjoys varying degrees of success, they can all classify themselves as serial entrepreneurs. And when you compare their careers to those who have only ever launched a single business, you begin to see just how noteworthy it is to be called a serial entrepreneur.

The Six Common Traits of Serial Entrepreneurs

Whether you’re looking at Branson, Kinney, Rubin, or anyone in between, you’ll notice that they all share some common traits. In particular, you’ll see the following:

1. Good Time Management

While it may not be the sexiest trait, good time management plays a crucial role in an entrepreneur’s ability to juggle multiple ventures at once. If you don’t have the ability to compartmentalize, tune in, tune out, and shift from one responsibility to another with little hesitation, you probably aren’t going to be capable of efficiently managing and growing multiple businesses.

Good time management comes across just as much in the little things as the big things. How do you react when your inbox reads “107 New Messages”? When you open up your Internet browser, do you immediately go to Facebook or are you focused on whatever you’re supposed to be doing? Can you schedule meetings throughout the day without compromising and overlapping? These are all positive signs of someone who stewards their time well.

2. Ability to Set Concrete Goals

There are soft goals and there are concrete goals. A soft goal is something like, “I want to be successful one day.” A concrete goal is something like, “I want to build a software company that generates $1 million in annual revenues by the end of 2018.”

Do you see the difference? One goal is totally arbitrary and vague, whereas the other has concrete measurements attached. Serial entrepreneurs set concrete goals because they understand that this is the only way to consistently accomplish tasks.

Learning how to set concrete goals takes time and a conscious effort. Many like to use the SMART goal-setting model, which stands for Specific, Measurable, Achievable, Relevant and Timely.

3. Strong Discipline

If you’re good at managing your time, then you’re probably a very disciplined individual. This is good, since discipline is an important component of being successful over and over again.

As an entrepreneur, you’re essentially your own boss. Sure, you may have investors and peers who hold you accountable, but you’re ultimately the one in charge. If you don’t have a driving force inside to stay on track, you’ll eventually falter and spiral out of control.

When you look at serial entrepreneurs like those mentioned in this article, you’ll notice that they all have a strong sense of discipline. They don’t need anyone else to tell them what to do or light a fire underneath them. They simply work hard because they have a desire to succeed.

4. Unwavering Optimism

It’s easy to look at someone like Richard Branson and think, “He sure has it made.” However, the truth is that even Richard Branson has encountered failures and setbacks. Regardless of how many companies you start and how much money you make, there will be times where everything will look bleak. They key here is to be optimistic.

Serial entrepreneurs have unwavering optimism that guides them through the highest of highs and the lowest of lows. This isn’t to say that they’re happy all the time, but rather that they don’t let circumstances dictate their future goals.

5. Creativity and Innovation

You can’t discuss entrepreneurship, and especially serial entrepreneurship, without mentioning creativity and innovation. In order to continuously churn out successful ideas, you have to think differently.

Unfortunately, this is one of those intrinsic things that you’re either born with or without. While you can surround yourself with people and things that spark creativity, you’re limited by the brain inside your head. Do you see things the way the world sees them, or do you look at situations differently?

6. Strong and Stable Leadership

You can’t grow multiple businesses without being able to lead people. While you can certainly hire good leaders to handle many of the different aspects of growth, you ultimately need the ability to lead these executives. Leadership can be learned to a degree, but it’s also a trait we’re born with.

Along these same lines, serial entrepreneurs are able to adopt new leadership strategies depending on the situation. What works with one business may not work for the next, and vice versa. Being able to shift leadership styles without compromising morals is a special characteristic to have.

Do You Have What it Takes?

Very few people have what it takes to be a serial entrepreneur. Even if you have the traits mentioned above, you also need the intangibles that are more difficult to quantify. And, of course, you can’t forget about the gratuitous amounts of luck that it takes to be in the right place at the right time.

However, the biggest key is that you don’t give up after failure. Research shows that nine out of ten startups will fail. That’s a strikingly poor success rate. You need the strength, patience, and fortitude to hang on when times get tough. Eventually, you’ll succeed, and that’s when you’ll build the confidence to do it all again.

Larry Alton

Larry Alton is a professional blogger, writer and researcher who contributes to a number of reputable online media outlets and news sources. A graduate of Des Moines University, he still lives in Iowa as a full-time freelance writer and avid news hound. Currently, Larry writes for Inquisitr.com, SocialMediaWeek.org, Tech.co, and SiteProNews.com among others. In addition to journalism, technical writing and in-depth research, he’s also active in his community and spends weekends volunteering with a local non-profit literacy organization and rock climbing.
He pursued his undergraduate degree in English Literature and transitioned to freelance writing full-time upon graduation. The years he spent studying and working the corporate daily grind prepared him well for his work with AGBeat.com, Entrepreneur.com, Mediapost.com and Americanthinker.com. A featured writer with Desk.com, WishPon.com and Experts.AllBusiness.com, he’s positioned himself at the top of the tech writing field and is known for “translating” industry jargon into easily digestible, readable content.
Particularly interesting fields for Larry include digital media, thought leadership, any and all things Android and iOS, entrepreneurship and social media. Connect with Larry on Google+ or in the comments section on any of the sites where he’s featured.

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